Water → HCID 10539784, Verbindung

HRID 47055Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 47055
[CH3:1][N:2]1[C:16]2[C:17]3[C:4]([CH2:5][C@@H:6]4[C:11]([C:12]=3[CH:13]=[CH:14][CH:15]=2)=[CH:10][C@@H:9]([CH2:18][N:19]=[N+]=[N-])[CH2:8][N:7]4[CH3:22])=[CH:3]1.[BH4-].[Na+].O>C(O)(C)C>[CH3:1][N:2]1[C:16]2[C:17]3[C:4]([CH2:5][C@@H:6]4[C:11]([C:12]=3[CH:13]=[CH:14][CH:15]=2)=[CH:10][C@@H:9]([CH2:18][NH2:19])[CH2:8][N:7]4[CH3:22])=[CH:3]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 4311764Sodium borohydride2×HCID 867367091,6-Dimethyl-8beta-azidomethyl-9, 10-didehydroergoline

Produkt 1

HCID 10539784HCID 10539784, VerbindungAusbeute 54,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

3.2 g 1,6-dimethyl-8β-azidomethyl-9, 10-didehydroergoline in 150 mls of isopropyl alcohol are treated with 6.4 g NaBH4 and heated to reflux under stirring and under nitrogen atmosphere for 24 hours. After this time further 2 g of NaBH4 are added and the heating is continued for 24 hours more. The reaction mixture is poured into water and extracted with chloroform. The chloroform extract is chromatographed onto SiO2 and the product is eluted with CH2Cl2 /MeOH/NH4OH (9/1/0.5). 1.6 g of 1,6-dimethyl-8β-aminomethyl-9, 10-didehydroergoline are thus obtained.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux
  3. waitthe heating is continued for 24 hours
  4. extractionextracted with chloroform
  5. extractionThe chloroform extract
  6. customis chromatographed onto SiO2
  7. washthe product is eluted with CH2Cl2 /MeOH/NH4OH (9/1/0.5)

Quellen und Nachweise

ORD-Eintrag
ord-643e6bd49d9e4e7c9555a88a8804197e
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04176182

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